A Memorable Visit to Chicago: Baseball, Art Deco, and Hidden Gems

My recent loss of a dear friend, Tim Reisen, reminded me of an extraordinary trip I once took to Chicago, Illinois. Tim was the kind of friend who would give you the shirt off his back—thoughtful, caring, and always passionate about his love for cars and racing. While he will be missed, I like to imagine him finding that perfect speedway in the sky. Rest in peace, Tim.

Chicago holds a special place in the heart of American sports fans, especially for those who love baseball. Baseball is ingrained in the soul of Americana, and once you experience it, there’s no shaking the love for the game. I’ve always dreamed of visiting the great ballparks before they disappear, like Yankee Stadium, "The House that Ruth Built," which was torn down in 2010 (sadly, I missed that one). Only two iconic fields remain: Fenway Park in Boston and Wrigley Field in Chicago.

A Last-Minute Trip to Chicago

When my daughter, who lives in Minneapolis, called and invited me to meet her in Chicago for a Cubs game, I didn’t hesitate. I hopped on the first flight from LAX to Chicago’s O'Hare Airport, but before I could go, I needed a place to stay. After scouring the internet, I discovered “The Robey,” https://www.therobey.com/ a gem of a hotel located in Chicago's trendy Wicker Park.

The Robey

2018 West North Avenue, Chicago, USA

Wicker Park Neighborhood

I found an inexpensive flight to O'Hare and eagerly Googled directions to The Robey. As I arrived in Chicago, the city's energy hit me, especially as I made my way to the "L" train, a quintessential Chicago experience. The Blue Line whisked me from O'Hare toward Wicker Park, and I exited at the Damen Avenue station. The platform was wonderfully old and vintage, with wooden planks and gooseneck lamps that gave it the feel of an old movie set.

The Hotel Experience

A short walk from the station brought me to The Robey Hotel, a stunning Art Deco building that towers over the intersection of Damen, Milwaukee, and North Avenue. The Robey was built in 1929, and it effortlessly blends old-world elegance with the bustling, modern vibe of Wicker Park.

My room was a nostalgic throwback. The entry door was a glass-paneled, wooden office door with the number "007" painted on the glass—just like something out of a Humphrey Bogart film. Inside, the room was modern yet retained a retro charm, perfect for anyone who appreciates Art Deco design.

Hidden Treasures in Wicker Park

From my window, I noticed a rooftop across the street with a ceiling that resembled Tiffany-stained glass. Curiosity got the better of me, so I headed to The Robey's rooftop terrace to get a better look. It was beautiful, and I decided to venture out to explore.

To my surprise, the building across the street was a Walgreens! But not just any Walgreens—this was a hidden architectural treasure https://blockclubchicago.org/2022/12/29/wicker-park-walgreens-with-iconic-vitamin-vault-closing-early-next-year/. Inside, the ceiling had a Star of David pattern with stained glass inlaid in hexagonal frames. Even more surprising was the discovery of a massive old bank vault on the lower level, now repurposed as the "Vitamin Vault," with rows of safe deposit boxes lining the walls. It was a delightful piece of Chicago history, hiding in plain sight.

Exploring the Neighborhood

Wicker Park and neighboring Bucktown turned out to be some of Chicago’s trendiest neighborhoods. Both areas are filled with lively clubs, dive bars, speakeasies, and late-night pubs. You could spend hours wandering the streets, exploring art galleries, boutiques, and hole-in-the-wall eateries that make this area vibrant and unique.

A Weekend in Chicago: Baseball, Banter, and Iconic Sights

Meeting up with my daughter and her fiancé at The Robey the next day was the perfect start to our Chicago adventure. After catching up over breakfast, we grabbed an Uber and headed straight for Wrigley Field to watch the Cubs face off against the Milwaukee Brewers. Our seats were prime—right by left field, down the third baseline, giving us a clear view of all the action.

Wrigley Field is more than just a ballpark; it's a time capsule of American sports history, and you can feel the weight of its legacy as soon as you step inside. I’d always heard about the infamous heckling from Cubs fans, but nothing quite prepared me for the banter my future son-in-law unleashed on the Brewers’ left fielder. His good-natured ribbing, shouted with perfect comedic timing, caught the attention of the entire section. And then, to our amazement, the Brewers’ left fielder turned around and cracked a smile, acknowledging the razzing with a tip of the hat.

But it wasn’t all taunting. My son-in-law was just as eager to praise the Cubs' left fielder, which eventually earned us a reward—a baseball tossed right into our section! That moment felt like the quintessential Wrigley experience: laughter, sportsmanship, and memories being made all around.

The following day, we shifted gears and took on the role of classic Chicago tourists. Millennium Park was our first stop, where we couldn’t resist taking Cloud Gate, affectionately known as "The Bean." It’s one of those landmarks you’ve seen in countless movies and Instagram posts, but nothing beats seeing its smooth, reflective surface up close. From there, we headed to Buckingham Fountain, instantly sparking a nostalgic hum of the *Married with Children* theme song as we admired the fountain’s grandeur.

We spent the rest of the day strolling through Chicago’s downtown, checking off bucket-list landmarks and soaking in the city’s iconic skyline. There’s something about Chicago that feels both monumental and familiar, probably because its landmarks are woven into the fabric of American pop culture.

By the end of the weekend, we left with new memories, shared laughs, and a possible new Cubs fan in the family! Chicago, with its unique blend of sports, history, and iconic sights, definitely left a lasting impression on all of us. Whether you’re there to catch a game at Wrigley or to immerse yourself in the city’s vibrant atmosphere, Chicago promises an unforgettable experience.

Chicago will forever be tied to both memories of friendship and the joy of baseball. If you're planning a trip to the Windy City, make sure to catch a Cubs game at Wrigley Field and experience the charm of Wicker Park—especially The Robey. Whether you're a history buff, a lover of architecture, or simply someone looking for a good time, Chicago has a bit of magic waiting for everyone.